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Oahu Vacation Packages

Oahu, "The Gathering Place," is home to Honolulu, Hawaii's largest city. Iconic Waikiki dazzles with its classic beaches, exciting nightlife and world-class cuisine. The North Shore is a surfer's paradise, home to the Banzai pipeline and scenic rainforests, offering a laid-back island style visitors are sure to enjoy. To the West, Pearl Harbor is rich in history with its WWII memorials and massive ships. Throughout the island a fusion of asian, polynesian and western culture give Oahu a flavor all its own. Enjoy the best deals to Oahu with our Hawaii vacation packages.

Time to Celebrate! – The BEST Offers in Hawaii

Book by 12/31/23 for select travel through 01/03/25

'Alohilani Resort Waikiki Beach

Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

Named among the Best Resorts in Hawaii in the 2022 Condé Nast Readers' Choice Awards, this family-friendly resort across from Waikiki Beach is within easy walking distance of shops, restaurants, and attractions.

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Waikiki Beach Marriott Resort & Spa

Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

Treat yourself to a luxury escape in Honolulu at the completely transformed Waikiki Beach Marriott Resort & Spa, a beachfront hotel with unparalleled service, thoughtful amenities and sweeping views of the Pacific Ocean.

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The Twin Fin

Waikiki, Oahu Our 4-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway.

Affording breathtaking views of iconic Diamond Head and steps from Waikiki Beach, this this lively hotel with an urban-Hawaiian vibe invites guests to embrace the Aloha Spirit with daily activities, regional cuisine and live entertainment.

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Hilton Hawaiian Village Waikiki Beach Resort

Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

Lush grounds, six spectacular pools, a beachfront lagoon, waterfalls and an array of shops and restaurants are all part of the "Village" experience at this expansive resort.

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Moana Surfrider, A Westin Resort & Spa

Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

This legendary resort, "The First Lady of Waikiki," combines turn-of the-century Victorian elegance with modern Westin amenities and luxuries.

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OUTRIGGER Waikiki Beach Resort

Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

Escape to sun, sand & surf on legendary Waikiki Beach. From the beach boys to Duke's Waikiki you experience beach life with live music and entertainment, vibrant cultural events, and accommodations overlooking iconic Waikiki Beach and Diamond Head.

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OUTRIGGER Reef Waikiki Beach Resort

Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

This distinctive, refined hotel presents a new vision of hospitality, combining timeless traditions with modern elegance.

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Embassy Suites by Hilton Waikiki Beach Walk

Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

This hotel featuring 1 & 2-bedroom suites offers spacious and comfortable accommodations just a short walk from Waikiki Beach. Free daily breakfast included.

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Sheraton Princess Kaiulani

Waikiki, Oahu Our 3.5-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

Experience comfort and relaxation in the heart of Waikiki at this hotel while enjoying an exceptional vacation value.

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Park Shore Waikiki

Waikiki, Oahu Our 3-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort.

Fronting Waikiki Beach, this hotel features magnificent ocean views and innumerable conveniences.

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OUTRIGGER Waikiki Beachcomber Hotel

Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

Steps from the beach, Hawaii's only handcrafted Hotel in the Heart of Waikiki. Curated by local artists and influencers, inspiring beach, culture, and art. Infused stylish hotel rooms and suites with unique personality and culture of the island.

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Prince Waikiki

Waikiki, Oahu Our 4-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway.

At this AAA Four-Diamond oceanfront hotel with all ocean-view accommodations, guests will delight in spacious rooms and suites with floor-to-ceiling windows, an exclusive Club Lounge, distinct cuisine and an adults-only infinity pool.

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OHANA Waikiki East by OUTRIGGER

Waikiki, Oahu Our 3-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort.

Discover exceptional value at this family-friendly hotel offering 1- and 2-bedroom suites with kitchenettes in the heart of Waikiki, just five minutes from the beach.

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DoubleTree by Hilton Alana Waikiki Beach

Waikiki, Oahu Our 3.5-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

This intimate boutique hotel is set at the gateway to Waikiki, just a short walk from the beach, and offers suites and tastefully appointed rooms.

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Hotel La Croix

Waikiki, Oahu Our 3.5-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

Situated in a dazzling location, just steps from luxury row, enjoy luxurious comforts and glittering ocean views at Hotel La Croix.

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Romer Waikiki at The Ambassador

Waikiki, Oahu Our 3.5-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

Centered around Waikiki’s creative culture, Romer’s easygoing guest rooms feature private lanais, plenty of lounge space, and locally sourced and roasted Big Island coffee.

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Time to Celebrate Hawaii Offer: Offers vary by hotel and travel dates and may be category-specific, require advance booking, be restricted to specific days of the week and/or require a minimum night stay. Booking and travel dates vary by hotel. Certain restrictions and blackout dates may apply. This offer is based on availability and can be modified or closed out at any time.

Rates quoted are per person, based on double occupancy unless otherwise stated. Rates for other travel dates may vary. Rates, terms, conditions and itinerary are subject to availability. Certain restrictions apply. Rates shown include government-imposed fees and taxes. Airline fees for optional services, including, but not limited to, baggage fees, may apply. Airline tickets are non-refundable and subject to airline change/cancellation penalties and rules, including pre-flight notification deadlines. Fees and policies vary among airlines and are subject to change without notice. Please contact the airline directly for details and answers to specific questions you may have. Additional restrictions apply. Advertised rates do not include any applicable daily resort or facility fees payable directly to the hotel operator at check-out; such fee amounts will be advised at the time of booking. Where applicable, kids stay free in same room as adults using existing bedding. Occupancy limits apply. Where applicable, kids eat free with full paying adult. Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]